US4371699A - Process for preparation of optically active N-mercaptoalkanoylamino acids - Google Patents

Process for preparation of optically active N-mercaptoalkanoylamino acids Download PDF

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Publication number
US4371699A
US4371699A US06/214,780 US21478080A US4371699A US 4371699 A US4371699 A US 4371699A US 21478080 A US21478080 A US 21478080A US 4371699 A US4371699 A US 4371699A
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US
United States
Prior art keywords
acid
optically active
process according
iii
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US06/214,780
Other languages
English (en)
Inventor
Takehisa Ohashi
Masami Shimazaki
Kazunori Kan
Hideo Kondo
Kiyoshi Watanabe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kanegafuchi Chemical Industry Co Ltd
Original Assignee
Kanegafuchi Chemical Industry Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP16237779A external-priority patent/JPS5686152A/ja
Priority claimed from JP16237879A external-priority patent/JPS56108734A/ja
Priority claimed from JP17190479A external-priority patent/JPS5695178A/ja
Priority claimed from JP2943080A external-priority patent/JPS56125363A/ja
Application filed by Kanegafuchi Chemical Industry Co Ltd filed Critical Kanegafuchi Chemical Industry Co Ltd
Assigned to KANEGAFUCHI CHEMICAL INDUSTRY COMPANY, LIMITED reassignment KANEGAFUCHI CHEMICAL INDUSTRY COMPANY, LIMITED ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: KAN KAZUNORI, KONDO HIDEO, OHHASHI TAKEHISA, SHIMAZAKI MASAMI, WATANABE KIYOSHI
Application granted granted Critical
Publication of US4371699A publication Critical patent/US4371699A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
US06/214,780 1979-12-13 1980-12-09 Process for preparation of optically active N-mercaptoalkanoylamino acids Expired - Lifetime US4371699A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP16237779A JPS5686152A (en) 1979-12-13 1979-12-13 Preparation of n-mercaptoacylamino acid
JP54-162377 1979-12-13
JP16237879A JPS56108734A (en) 1979-12-13 1979-12-13 Preparation of beta-halogenoisobutyryl halide
JP54-162378 1979-12-13
JP17190479A JPS5695178A (en) 1979-12-28 1979-12-28 Production of n-mercaptoalkanoylaminoacid
JP54-171904 1979-12-28
JP2943080A JPS56125363A (en) 1980-03-08 1980-03-08 Preparation of thiol compound
JP55-29430 1980-03-08

Publications (1)

Publication Number Publication Date
US4371699A true US4371699A (en) 1983-02-01

Family

ID=27459067

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/214,780 Expired - Lifetime US4371699A (en) 1979-12-13 1980-12-09 Process for preparation of optically active N-mercaptoalkanoylamino acids

Country Status (8)

Country Link
US (1) US4371699A (it)
DE (1) DE3046271A1 (it)
ES (1) ES497665A0 (it)
FR (1) FR2471975B1 (it)
GB (1) GB2065643B (it)
IE (1) IE50548B1 (it)
IT (1) IT1188971B (it)
NL (1) NL192264C (it)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4428940A (en) 1981-03-12 1984-01-31 Beecham Group P.L.C. Anti-hypertensive compounds and compositions
US4499102A (en) * 1979-12-13 1985-02-12 Santen Pharmaceutical Co., Ltd. Thiazolidine and pyrrolidine compounds and pharmaceutical compositions containing them
US4578480A (en) * 1980-02-26 1986-03-25 John Wyeth & Brother Limited Process for preparing 1-(3-bromo-2-alkylpropanoyl)-L-proline derivatives
US4596819A (en) * 1984-01-23 1986-06-24 Warner-Lambert Company Modified tripeptides
US5312826A (en) * 1991-06-21 1994-05-17 Tanabe Seiyaku Co., Ltd. N,3-disubstituted alaninamide derivatives
US5523313A (en) * 1992-12-28 1996-06-04 Tanabe Seiyaku Co., Ltd. Indole-containing peptide and process for preparing the same
WO2001055074A1 (fr) * 2000-01-25 2001-08-02 Kaneka Corporation Processus de production d'acide carboxylique optiquement actif substitue en position 2
US20050136666A1 (en) * 2003-12-23 2005-06-23 Tokyo Electron Limited Method and apparatus for etching an organic layer

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3143726A1 (de) * 1981-11-04 1983-05-11 Degussa Ag, 6000 Frankfurt Optisch aktive prolin-derivate, verfahren zu ihrer herstellung und ihre verwendung
US4634716A (en) * 1982-09-30 1987-01-06 Merck & Co., Inc. Substituted N-carboxymethyl-aminoacylaminoalkanoic acids useful as antihypertensive agents
KR860001391B1 (ko) * 1984-07-23 1986-09-22 보령제약 주식회사 피롤리딘 유도체의 제조방법
KR870001570B1 (ko) * 1984-12-19 1987-09-04 보령제약 주식회사 피롤리딘 유도체의 제조방법
KR870001569B1 (ko) * 1985-02-11 1987-09-04 보령제약 주식회사 피롤리딘 유도체의 제조방법
AT395012B (de) * 1986-06-27 1992-08-25 Richter Gedeon Vegyeszet Verfahren zur herstellung von n-(1(s)|thoxycarbonyl-3-phenyl-propyl)-(s)-alanyl-(s)prolin und von dessen saeureadditionssalzen

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046889A (en) * 1976-02-13 1977-09-06 E. R. Squibb & Sons, Inc. Azetidine-2-carboxylic acid derivatives
US4070361A (en) * 1977-04-21 1978-01-24 E. R. Squibb & Sons, Inc. Mercaptoalkylsulfonyl proline and pipecolic acid and esters thereof
US4105776A (en) * 1976-06-21 1978-08-08 E. R. Squibb & Sons, Inc. Proline derivatives and related compounds
US4192878A (en) * 1976-12-03 1980-03-11 E. R. Squibb & Sons, Inc. Derivatives of thiazolidinecarboxylic acids and related acids

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU509899B2 (en) * 1976-02-13 1980-05-29 E.R. Squibb & Sons, Inc. Proline derivatives and related compounds
US4108886A (en) * 1977-03-11 1978-08-22 E. R. Squibb & Sons, Inc. Thiopropanoylamino acid derivatives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046889A (en) * 1976-02-13 1977-09-06 E. R. Squibb & Sons, Inc. Azetidine-2-carboxylic acid derivatives
US4105776A (en) * 1976-06-21 1978-08-08 E. R. Squibb & Sons, Inc. Proline derivatives and related compounds
US4192878A (en) * 1976-12-03 1980-03-11 E. R. Squibb & Sons, Inc. Derivatives of thiazolidinecarboxylic acids and related acids
US4070361A (en) * 1977-04-21 1978-01-24 E. R. Squibb & Sons, Inc. Mercaptoalkylsulfonyl proline and pipecolic acid and esters thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Morrison et al.; Organic Chemistry, pp. 525 and 590, (1969). *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4499102A (en) * 1979-12-13 1985-02-12 Santen Pharmaceutical Co., Ltd. Thiazolidine and pyrrolidine compounds and pharmaceutical compositions containing them
US4578480A (en) * 1980-02-26 1986-03-25 John Wyeth & Brother Limited Process for preparing 1-(3-bromo-2-alkylpropanoyl)-L-proline derivatives
US4428940A (en) 1981-03-12 1984-01-31 Beecham Group P.L.C. Anti-hypertensive compounds and compositions
US4596819A (en) * 1984-01-23 1986-06-24 Warner-Lambert Company Modified tripeptides
US5312826A (en) * 1991-06-21 1994-05-17 Tanabe Seiyaku Co., Ltd. N,3-disubstituted alaninamide derivatives
US5523313A (en) * 1992-12-28 1996-06-04 Tanabe Seiyaku Co., Ltd. Indole-containing peptide and process for preparing the same
WO2001055074A1 (fr) * 2000-01-25 2001-08-02 Kaneka Corporation Processus de production d'acide carboxylique optiquement actif substitue en position 2
US20030144546A1 (en) * 2000-01-25 2003-07-31 Susumu Amano Process for producing optically active carboxylic acid subtituted in 2-position
US20060247470A1 (en) * 2000-01-25 2006-11-02 Kaneka Corporation Process for producing optically active carboxylic acid substituted in 2-position
US20050136666A1 (en) * 2003-12-23 2005-06-23 Tokyo Electron Limited Method and apparatus for etching an organic layer

Also Published As

Publication number Publication date
FR2471975A1 (fr) 1981-06-26
IT1188971B (it) 1988-01-28
GB2065643A (en) 1981-07-01
FR2471975B1 (fr) 1985-07-05
IT8050342A0 (it) 1980-12-11
DE3046271C2 (it) 1988-07-28
IT8050342A1 (it) 1982-06-11
NL192264B (nl) 1996-12-02
IE802603L (en) 1981-06-13
ES8200863A1 (es) 1981-11-16
IE50548B1 (en) 1986-05-14
GB2065643B (en) 1983-08-24
NL8006768A (nl) 1981-07-16
ES497665A0 (es) 1981-11-16
NL192264C (nl) 1997-04-03
DE3046271A1 (de) 1981-08-27

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